US8637542B2 - Kinase inhibitors and methods of use - Google Patents
Kinase inhibitors and methods of use Download PDFInfo
- Publication number
- US8637542B2 US8637542B2 US12/920,970 US92097009A US8637542B2 US 8637542 B2 US8637542 B2 US 8637542B2 US 92097009 A US92097009 A US 92097009A US 8637542 B2 US8637542 B2 US 8637542B2
- Authority
- US
- United States
- Prior art keywords
- alkyl
- limited
- cycloalkyl
- aryl
- alkenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- QTQMXWHCEHOMGY-UHFFFAOYSA-N CCNc1nc2cc(C(C)(C)C)ccc2[o]1 Chemical compound CCNc1nc2cc(C(C)(C)C)ccc2[o]1 QTQMXWHCEHOMGY-UHFFFAOYSA-N 0.000 description 1
- VSRPOIGWIINJAD-UHFFFAOYSA-N CN1C=CC2=C1/C=C\C(C(C)(C)C)=C/2 Chemical compound CN1C=CC2=C1/C=C\C(C(C)(C)C)=C/2 VSRPOIGWIINJAD-UHFFFAOYSA-N 0.000 description 1
- GNVOKVQNPSRKJD-UHFFFAOYSA-N CN1CCC(N2CCN(C(C)(C)C)CC2)CC1 Chemical compound CN1CCC(N2CCN(C(C)(C)C)CC2)CC1 GNVOKVQNPSRKJD-UHFFFAOYSA-N 0.000 description 1
- DEMGFMRQQZQFBO-UHFFFAOYSA-N CN1CCC(NC(C)(C)C)CC1 Chemical compound CN1CCC(NC(C)(C)C)CC1 DEMGFMRQQZQFBO-UHFFFAOYSA-N 0.000 description 1
- UAJLNIPWJQINPL-UHFFFAOYSA-N CN1CCN(C(=O)C(C)(C)C)CC1 Chemical compound CN1CCN(C(=O)C(C)(C)C)CC1 UAJLNIPWJQINPL-UHFFFAOYSA-N 0.000 description 1
- WAKNQQVWPGKEKU-UHFFFAOYSA-N CN1CCN(C(C)(C)C)CC1 Chemical compound CN1CCN(C(C)(C)C)CC1 WAKNQQVWPGKEKU-UHFFFAOYSA-N 0.000 description 1
- FAYYGBYAEGGOSJ-UHFFFAOYSA-N CN1CCN(C2=NC=C(C(C)(C)C)C=C2)CC1 Chemical compound CN1CCN(C2=NC=C(C(C)(C)C)C=C2)CC1 FAYYGBYAEGGOSJ-UHFFFAOYSA-N 0.000 description 1
- INCHMACXOBORTB-UHFFFAOYSA-N CN1CCN(C2=NC=CC(C(C)(C)C)=C2)CC1 Chemical compound CN1CCN(C2=NC=CC(C(C)(C)C)=C2)CC1 INCHMACXOBORTB-UHFFFAOYSA-N 0.000 description 1
- IAMFGQFKKPBQAQ-UHFFFAOYSA-N CN1CCN(CC2=CN=C(C(C)(C)C)C=C2)CC1 Chemical compound CN1CCN(CC2=CN=C(C(C)(C)C)C=C2)CC1 IAMFGQFKKPBQAQ-UHFFFAOYSA-N 0.000 description 1
- SVPGZFUBDNHJBM-UHFFFAOYSA-N CN1CCN(CCOC(C)(C)C)CC1 Chemical compound CN1CCN(CCOC(C)(C)C)CC1 SVPGZFUBDNHJBM-UHFFFAOYSA-N 0.000 description 1
- QZPFLLDEOOKPGS-UHFFFAOYSA-N CNC1CC(C(C)(C)C)C1 Chemical compound CNC1CC(C(C)(C)C)C1 QZPFLLDEOOKPGS-UHFFFAOYSA-N 0.000 description 1
- GQAFHICLWYMCJB-UHFFFAOYSA-N CNCCN1CCN(C(C)=O)CC1 Chemical compound CNCCN1CCN(C(C)=O)CC1 GQAFHICLWYMCJB-UHFFFAOYSA-N 0.000 description 1
- FFRIQXXYTNLUKG-UHFFFAOYSA-N CO/C1=C/C=C(/Br)C2=C1NC(C(C)(C)C)=C2 Chemical compound CO/C1=C/C=C(/Br)C2=C1NC(C(C)(C)C)=C2 FFRIQXXYTNLUKG-UHFFFAOYSA-N 0.000 description 1
- MGIQFSMACWDGTP-UHFFFAOYSA-N CO/C1=C/C=C(/OC)C2=C1C=C(C(C)(C)C)N2 Chemical compound CO/C1=C/C=C(/OC)C2=C1C=C(C(C)(C)C)N2 MGIQFSMACWDGTP-UHFFFAOYSA-N 0.000 description 1
- DISRKJKRVIIMAL-UHFFFAOYSA-N CO/C1=C/C=C\C2=C1NC(C(C)(C)C)=C2 Chemical compound CO/C1=C/C=C\C2=C1NC(C(C)(C)C)=C2 DISRKJKRVIIMAL-UHFFFAOYSA-N 0.000 description 1
- DFRJPQORPUYQTB-UHFFFAOYSA-N COC1=CC(Br)=CC(C(C)(C)C)=C1 Chemical compound COC1=CC(Br)=CC(C(C)(C)C)=C1 DFRJPQORPUYQTB-UHFFFAOYSA-N 0.000 description 1
- BFGULKASDQXIPQ-UHFFFAOYSA-N COC1=CC=C(/C2=C/C=C\C3=C2NC(C(C)(C)C)=C3)C=C1 Chemical compound COC1=CC=C(/C2=C/C=C\C3=C2NC(C(C)(C)C)=C3)C=C1 BFGULKASDQXIPQ-UHFFFAOYSA-N 0.000 description 1
- GRPQHNMWTKWJIU-UHFFFAOYSA-N COCOC1=C(Br)C=CC(C(C)(C)C)=C1 Chemical compound COCOC1=C(Br)C=CC(C(C)(C)C)=C1 GRPQHNMWTKWJIU-UHFFFAOYSA-N 0.000 description 1
- ZNRVRWHPZZOTIE-SSDOTTSWSA-N C[C@@H](CO)CC(C)(C)C Chemical compound C[C@@H](CO)CC(C)(C)C ZNRVRWHPZZOTIE-SSDOTTSWSA-N 0.000 description 1
- ZNRVRWHPZZOTIE-ZETCQYMHSA-N C[C@H](CO)CC(C)(C)C Chemical compound C[C@H](CO)CC(C)(C)C ZNRVRWHPZZOTIE-ZETCQYMHSA-N 0.000 description 1
- DXKYIWXTRRJEOL-UHFFFAOYSA-N [C-]#[N+]C1=CC(C(C)(C)C)=CC=C1F Chemical compound [C-]#[N+]C1=CC(C(C)(C)C)=CC=C1F DXKYIWXTRRJEOL-UHFFFAOYSA-N 0.000 description 1
- YOWNZDZQEJKLEY-UHFFFAOYSA-N [H]C(=O)C1=C(C)C=C(C(C)(C)C)S1 Chemical compound [H]C(=O)C1=C(C)C=C(C(C)(C)C)S1 YOWNZDZQEJKLEY-UHFFFAOYSA-N 0.000 description 1
- MYRSXBLGFWAINF-UHFFFAOYSA-N [H]C(=O)C1=CC2=C(C=C1)SC(C(C)(C)C)=C2 Chemical compound [H]C(=O)C1=CC2=C(C=C1)SC(C(C)(C)C)=C2 MYRSXBLGFWAINF-UHFFFAOYSA-N 0.000 description 1
- NUFAUQKKPHWSSQ-UHFFFAOYSA-N [H]C(=O)C1=CNC2=C1/C=C\C(C(C)(C)C)=C/2 Chemical compound [H]C(=O)C1=CNC2=C1/C=C\C(C(C)(C)C)=C/2 NUFAUQKKPHWSSQ-UHFFFAOYSA-N 0.000 description 1
- PGVCNHZRBGLFLD-UHFFFAOYSA-N [H]C(=O)C1=COC(C(C)(C)C)=C1 Chemical compound [H]C(=O)C1=COC(C(C)(C)C)=C1 PGVCNHZRBGLFLD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Abstract
Description
TABLE A |
The following includes exemplary core structures of the present invention wherein X1, X2, and X3 are |
unsubstituted carbon or substituted carbon, or unsubtituted N or substituted N. |
(ii) Name of unsubstituted | (iv) Name of unsubstituted | ||
(i) Structure | core, including amino group | (iii) Structure | core, including amino group |
|
(vi) 1H-Pyrrolo[3,2-c] pyridin-4-ylamine |
|
(viii) 1H-Pyrrolo[2,3-d] pyridazin-4-ylamine |
|
(x) 2H-Pyrrolo[3,4-c] pyridin-4-ylamine |
|
(xii) Pyrrolo[1,2-c]- pyrimidin-1 ylamine |
|
(xiv) 6H-Pyrrolo[3,4-d]- pyridazin-4-ylamine |
|
(xvi) Pyrrolo[1,2-d]- [1,2,4]triazin-4-ylamine |
|
(xviii) Imidazo[1,5-c] pyridazin-5-ylamine |
|
(xx) 1H-Pyrazolo[4,3-c] pyridin-4-ylamine |
|
(xxii) Imidazo[1,5-d]- [1,2,4]triazin-4- ylamine | ||
-
- X1 is independently N or C-E1;
wherein W1, W2, and W7 are independently N or C—R5; W4 and W10 are independently N—R5, O, or S; W5, W6, W8, and W9 are independently N or C—R5; and W3 is C or N, provided no more than two N and/or N—R5 are adjacent and no two O or S are adjacent.
wherein R′5 is —(W1)k—R53 or R55; k is 0 or 1, n is 0, 1, 2, or 3, and —(W1)k—R53 and R55 are as defined above.
wherein R′5 is —(W1)k—R53 or R55; k is 0 or 1, n is 0, 1, 2, or 3, and —(W1)k—R53 and R55 are as defined above
wherein W12, W13, W14, and W15 are independently N or C—R5; W11 and W18 are independently N—R5, O, or S; W16 and W17 are independently N or C—R5; provided no more than two N are adjacent.
wherein X11, X12, X13, X14, X15, X16, and X17 are independently N, or C—R5; provided that no more than two N are adjacent.
wherein R′5 is —(W1)k—R53 or R55; k is 0 or 1, n is 0, 1, 2, or 3, and (W1)k—R53 and R55 are as defined above. In some embodiments of the compounds of Formula XVIII-A, Formula XVIII-B, or Formula XVIII-C, R5 is —NR31R32, —NR31C(═O)R32, —NR31S(O)0-2R32, or —NR34R35. In some embodiments, R5 is NH2. In some embodiments, n is 0.
wherein R′5 is —(W1)k—R53 or R55; k is 0 or 1, and —(W1)k—R53 and R55 are as defined above. In some embodiments of the compounds of Formula XVIII-A, Formula XVIII-B, or Formula XVIII-C, R5 is —NR31R32, —NR31C(═O)R32, —NR31S(O)0-2R32, or —NR34R35. In some embodiments, R5 is —NH2. In some embodiments, n is 0.
wherein X14 and X16, are N, and X13, is C—R5; or X14 is N, and X13 and X16, are C—R5; or X13 and X14, are N, and X16, is C—R5.
wherein R′5 is —(W1)k—R53 or R55; k is 0 or 1, n is 0, 1, 2, or 3; and —(W1)k—R53 and R55 are as defined above. In some embodiments of the compounds of Formula XX-A or Formula XX-B, R5 is —NR31R32, —NR31C(═O)R32, —NR31S(O)0-2R32, or —NR34R35. In some embodiments, R5 is —NH2. In some embodiments, n is 0.
M1 is a 5-10 membered ring system, wherein the ring system is monocyclic or bicyclic; R1 and R2 are independently H, -L-alkyl, -L-cycloalkyl, L-alkylcycloalkyl, -L-aryl, -L-heteroaryl, L-alkylaryl, -L-alkylheteroaryl, -L-alkylheterocyclyl, -L-alkenyl, -L-alkynyl, L-_alkenylcycloalkyl, -L-alkynylcycloalkyl, -L-heterocyclyl, wherein each alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, or alkynyl moiety is unsubstituted or is substituted by one or more independent R3 substituents; L is absent, —C(O)—, —C(O)O—, —C(O)NR31—, —S—, —S(O)—, —S(O)2—, —S(O)2NR31—, or —NR31; X1 is independently N or C-E1; X2 is NH, X3 is C, and X4 is C; or X2 is N, X3 is C, and X4 is N; or X2 is N, X3 is N, and X4 is N; or X2 is N, X3 is N, and X4 is C; or X2 is C-E1, X3 is N, and X4 is C; or X2 is C-E1, X3 is C, and X4 is N;
M1 is a 5-10 membered ring system, wherein the ring system is monocyclic or bicyclic; R1 and R2 are independently H, -L-alkyl, -L-cycloalkyl, L-alkylcycloalkyl, -L-aryl, -L-heteroaryl, L-alkylaryl, -L-alkylheteroaryl, -L-alkylheterocyclyl, -L-alkenyl, -L-alkynyl, L-_alkenylcycloalkyl, -L-alkynylcycloalkyl, -L-heterocyclyl, wherein each alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, or alkynyl moiety is unsubstituted or is substituted by one or more independent R3 substituents; L is absent, —C(O)—, —C(O)O—, —C(O)NR31—, —S—, —S(O)—, —S(O)2—, —S(O)2NR31—, or —NR31;
R1 and R2 are independently H, -L-alkyl, -L-cycloalkyl, L-alkylcycloalkyl, -L-aryl, -L-heteroaryl, L-alkylaryl, -L-alkylheteroaryl, -L-alkylheterocyclyl, -L-alkenyl, -L-alkynyl, L-_alkenylcycloalkyl, -L-alkynylcycloalkyl, -L-heterocyclyl, wherein each alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, or alkynyl moiety is unsubstituted or is substituted by one or more independent R3 substituents; L is absent, —C(O)—, —C(O)O—, —C(O)NR31—, —S—, —S(O)—, —S(O)2—, —S(O)2NR31—, or —NR31.
W4 is N—R5, O, or S, W5 is C—R5, and W6 is N or C—R5; W10 is N—R5, O, or S; W8 is N or C—R5; each R5 is independently —(W1)k—R53 or R55; k is 0 or 1; W1 is —O—, —NR6—, —S(O)0-2—, —C(O)—, —C(O)N(R6)—, —N(R6)C(O)—, —N(R6)S(O)—, —N(R6)S(O)2—, —C(O)O—, —CH(R6)N(C(O)OR7)—, —CH(R7)N(C(O)R7)—, —CH(R6)N(SO2R7)—, —CH(R6)N(R7)—, —CH(R6)C(O)N(R7)—, —CH(R6)N(R7)C(O)—, —CH(R6)N(R7)S(O)—, or CH(R6)N(R7)S(O)2;
W4 is N—R5, O, or S, and W6 is N, or W10 is N—R5, O, or S, and W8 is N;
R1 and R2 are independently H, -L-alkyl, -L-cycloalkyl, L-alkylcycloalkyl, -L-aryl, -L-heteroaryl, L-alkylaryl, -L-alkylheteroaryl, -L-alkylheterocyclyl, -L-alkenyl, -L-alkynyl, L-_alkenylcycloalkyl, -L-alkynylcycloalkyl, -L-heterocyclyl, wherein each alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, or alkynyl moiety is unsubstituted or is substituted by one or more independent R3 substituents; L is absent, —C(O)—, —C(O)O—, —C(O)NR31—, —S—, —S(O)—, —S(O)2—, —S(O)2NR31—, or —NR31;
R1 and R2 are independently H, -L-alkyl, -L-cycloalkyl, L-alkylcycloalkyl, -L-aryl, -L-heteroaryl, L-alkylaryl, -L-alkylheteroaryl, -L-alkylheterocyclyl, -L-alkenyl, -L-alkynyl, L-_alkenylcycloalkyl, -L-alkynylcycloalkyl, -L-heterocyclyl, wherein each alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, or alkynyl moiety is unsubstituted or is substituted by one or more independent R3 substituents; L is absent, —C(O)—, —C(O)O—, —C(O)NR31—, —S—, —S(O)—, —S(O)2—S(O)2NR31—, or —NR31.
R1 and R2 are independently H, -L-alkyl, -L-cycloalkyl, L-alkylcycloalkyl, -L-aryl, -L-heteroaryl, L-alkylaryl, -L-alkylheteroaryl, -L-alkylheterocyclyl, -L-alkenyl, -L-alkynyl, L-_alkenylcycloalkyl, -L-alkynylcycloalkyl, -L-heterocyclyl, wherein each alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, or alkynyl moiety is unsubstituted or is substituted by one or more independent R3 substituents; L is absent, —C(O)—, —C(O)O—, —C(O)NR31—, —S—, —S(O)—, —S(O)2—, —S(O)2NR31—, or —NR31.
wherein: X13 and X14 are N, and X16 is C—R5; or X14 and X16, are N, and X13 is C—R5; or X14 is N, and X13 and X16 are C—R5; each R5 is independently (W1)k—R53 or R55; k is 0 or 1; W1 is —O—, —NR6—, —S(O)0-2—, —C(O)—, —C(O)N(R6)—, —N(R6)C(O)—, —N(R6)S(O)—, —N(R6)S(O)2, —C(O)O , —CH(R6)N(C(O)OR7)—, —CH(R7)N(C(O)R7)—, —CH(R6)N(SO2R7)—, —CH(R6)N(R7)—, —CH(R6)C(O)N(R7)—, —CH(R6)N(R7)C(O)—, —CH(R6)N(R7)S(O)—, or —CH(R6)N(R7)S(O)2—;
wherein X14 and X16, are N, and X13, is C—R5; or X14 is N, and X13 and X16, are C—R5; or X13 and X14, are N, and X16, is C—R5;
R1 and R2 are independently H, -L-alkyl, -L-cycloalkyl, L-alkylcycloalkyl, -L-aryl, -L-heteroaryl, L-alkylaryl, -L-alkylheteroaryl, -L-alkylheterocyclyl, -L-alkenyl, -L-alkynyl, L-_alkenylcycloalkyl, -L-alkynylcycloalkyl, -L-heterocyclyl, wherein each alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, or alkynyl moiety is unsubstituted or is substituted by one or more independent R3 substituents; L is absent, —C(O)—, —C(O)O—, —C(O)NR31—, —S—, —S(O)—, —S(O)2—, —S(O)2NR31—, or —NR31;
wherein W11 is N—R5, O, or S, and W16 is N or C—R5; or W18 is N—R5, O, or S; and W17 is N or C—R5; each R5 is independently —(W1)k—R53 or R55; k is 0 or 1; W1 is —O—, —NR6—, —S(O)0-2—, —C(O)—, —C(O)N(R6)—, —N(R6)C(O)—, —N(R6)S(O)—, —N(R6)S(O)2—, —C(O)O—, —CH(R6)N(C(O)OR7)—, —CH(R7)N(C(O)R7)—, —CH(R6)N(SO2R7)—, —CH(R6)N(R7)—, —CH(R6)C(O)N(R7)—, —CH(R6)N(R7)C(O)—, —CH(R6)N(R7)S(O)—, or —CH(R6)N(R7)S(═)2—;
TABLE 1 |
Illustrative R1 moieties of the compounds of Formula I. |
Sub- | Sub- | ||
class # | R1 | class # | R1 |
R1-1 | H | R1-2 | Me |
iso-propyl | n-propyl | ||
R1-3 | Et iso-butyl | R1-4 |
|
R1-5 |
|
R1-6 |
|
R1-7 |
|
R1-8 |
|
R1-9 |
|
R1-10 |
|
R1-11 |
|
R1-12 |
|
R1-13 |
|
R1-14 |
|
R1-15 |
|
R1-16 |
|
R1-17 |
|
R1-18 |
|
R1-19 |
|
R1-20 |
|
R1-21 |
|
R1-22 |
|
R1-23 |
|
R1-24 |
|
R1-25 |
|
R1-26 |
|
R1-27 |
|
R1-28 |
|
R1-29 |
|
R1-30 |
|
R1-31 |
|
R1-32 |
|
R1-33 |
|
R1-34 |
|
R1-35 |
|
R1-36 |
|
R1-37 |
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R1-38 |
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R1-39 |
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R1-40 |
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R1-41 |
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R1-42 |
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R1-43 |
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R1-44 |
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R1-45 |
|
R1-46 |
|
TABLE 2 |
Illustrative R2 moieties of the compounds of Formula I. |
Sub- | Sub- | Sub- | |||
class # | R2 | class # | R2 | class # | R2 |
R2-1 | H | R2-2 | Me | R2-3 | Et |
R2-4 |
|
R2-5 |
|
R2-6 |
|
R2-7 |
|
R2-8 |
|
R2-9 |
|
R2-10 | iso-propyl | R2-11 | n-propyl | R2-12 | iso-butyl |
R2-13 | —F | R2-14 | —CN | R2-15 | —CF3 |
R2-16 | —OMe | R2-17 | —NHMe | R2-18 | —NHEt |
R2-19 |
|
R2-20 |
|
R2-21 |
|
R2-22 |
|
R2-23 |
|
R2-24 |
|
R2-25 |
|
R2-26 |
|
R2-27 |
|
R2-28 |
|
R2-29 |
|
R2-30 |
|
R2-31 |
|
R2-32 |
|
R2-33 |
|
R2-34 |
|
R2-35 |
|
R2-36 |
|
R2-37 |
|
R2-38 |
|
R2-39 |
|
R2-40 |
|
R2-41 |
|
R2-42 |
|
R2-43 |
|
R2-44 |
|
R2-45 |
|
R2-46 |
|
R2-47 |
|
R2-48 |
|
R2-49 |
|
R2-50 |
|
R2-51 |
|
R2-52 |
|
R2-53 |
|
R2-54 |
|
R2-55 |
|
R2-56 |
|
R2-57 |
|
R2-58 |
|
R2-59 |
|
R2-60 |
|
R2-61 |
|
R2-62 |
|
R2-63 |
|
R2-64 |
|
R2-65 |
|
R2-66 |
|
R2-67 |
|
R2-68 |
|
R2-69 |
|
R2-70 |
|
R2-71 |
|
R2-72 |
|
R2-73 |
|
R2-74 | —Cl | R2-75 |
|
R2-76 |
|
R2-77 |
|
R2-78 |
|
R2-79 |
|
R2-80 |
|
R2-81 |
|
R2-82 |
|
R2-83 |
|
R2-84 |
|
R2-85 |
|
R2-86 |
|
R2-87 |
|
R2-88 |
|
R2-89 |
|
R2-90 |
|
R2-91 |
|
||||
TABLE 3 |
Illustrative M1 moieties of the compounds of Formula I.: |
Sub- | Sub- | Sub- | |||
class # | M1 | class # | M1 | class # | M1 |
M1-1 |
|
M1-2 |
|
M1-3 |
|
M1-4 |
|
M1-5 |
|
M1-6 |
|
M1-7 |
|
M1-8 |
|
M1-9 |
|
M1-10 |
|
M1-11 |
|
M1-12 |
|
M1-13 |
|
M1-14 |
|
M1-15 |
|
M1-16 |
|
M1-17 |
|
M1-18 |
|
M1-19 |
|
M1-20 |
|
M1-21 |
|
M1-22 |
|
M1-23 |
|
M1-24 |
|
M1-25 |
|
M1-26 |
|
M1-27 |
|
M1-28 |
|
M1-29 |
|
M1-30 |
|
M1-31 |
|
M1-32 |
|
M1-33 |
|
M1-34 |
|
M1-35 |
|
M1-36 |
|
M1-37 |
|
M1-38 |
|
M1-39 |
|
M1-40 |
|
M1-41 |
|
M1-42 |
|
M1-43 |
|
M1-44 |
|
M1-45 |
|
M1-46 |
|
M1-47 |
|
M1-48 |
|
M1-49 |
|
M1-50 |
|
M1-51 |
|
M1-52 |
|
M1-53 |
|
M1-54 |
|
M1-55 |
|
M1-56 |
|
M1-57 |
|
M1-58 |
|
M1-59 |
|
M1-60 |
|
M1-61 |
|
M1-62 |
|
M1-63 |
|
M1-64 |
|
M1-65 |
|
M1-66 |
|
M1-67 |
|
M1-68 |
|
M1-69 |
|
M1-70 |
|
M1-71 |
|
M1-72 |
|
M1-73 |
|
M1-74 |
|
M1-75 |
|
M1-76 |
|
M1-77 |
|
M1-78 |
|
M1-79 |
|
M1-80 |
|
M1-81 |
|
M1-82 |
|
M1-83 |
|
M1-84 |
|
M1-85 |
|
M1-86 |
|
M1-87 |
|
M1-88 |
|
M1-89 |
|
M1-90 |
|
M1-91 |
|
M1-92 |
|
M1-93 |
|
M1-94 |
|
M1-95 |
|
M1-96 |
|
M1-97 |
|
M1-98 |
|
M1-99 |
|
M1-100 |
|
M1-101 |
|
M1-102 |
|
M1-103 |
|
M1-104 |
|
M1-105 |
|
M1-106 |
|
M1-107 |
|
M1-108 |
|
M1-109 |
|
M1-110 |
|
M1-111 |
|
M1-112 |
|
M1-113 |
|
M1-114 |
|
M1-115 |
|
M1-116 |
|
M1-117 |
|
M1-118 |
|
M1-119 |
|
M1-120 |
|
M1-121 |
|
M1-122 |
|
M1-123 |
|
M1-124 |
|
M1-125 |
|
M1-126 |
|
M1-127 |
|
M1-128 |
|
M1-129 |
|
M1-130 |
|
M1-131 |
|
M1-132 |
|
M1-133 |
|
M1-134 |
|
M1-135 |
|
M1-136 |
|
M1-137 |
|
M1-138 |
|
M1-139 |
|
M1-140 |
|
M1-141 |
|
M1-142 |
|
M1-143 |
|
M1-144 |
|
M1-145 |
|
M1-146 |
|
M1-147 |
|
M1-148 |
|
M1-149 |
|
M1-150 |
|
M1-151 |
|
M1-152 |
|
M1-153 |
|
M1-154 |
|
M1-155 |
|
M1-156 |
|
M1-157 |
|
M1-158 |
|
M1-159 |
|
M1-160 |
|
M1-161 |
|
M1-162 |
|
M1-163 |
|
M1-164 |
|
M1-165 |
|
M1-166 |
|
M1-167 |
|
M1-168 |
|
M1-169 |
|
M1-170 |
|
M1-171 |
|
M1-172 |
|
M1-173 |
|
M1-174 |
|
M1-175 |
|
M1-176 |
|
M1-177 |
|
M1-178 |
|
M1-179 |
|
M1-180 |
|
M1-181 |
|
M1-182 |
|
M1-183 |
|
M1-184 |
|
M1-185 |
|
M1-186 |
|
M1-187 |
|
M1-188 |
|
M1-189 |
|
M1-191 |
|
M1-192 |
|
M1-193 |
|
M1-194 |
|
M1-195 |
|
M1-196 |
|
M1-197 |
|
M1-198 |
|
M1-199 |
|
M1-200 |
|
M1-201 |
|
M1-202 |
|
M1-203 |
|
M1-204 |
|
M1-205 |
|
6 |
|
||||
TABLE 4 |
In-vitro IC50 activity of selected compounds of the invention in selected assays. |
mTORC | PI3K α | PI3K β | PI3K γ | PI3K δ | ||
Structure | IC50 (nM) | IC50 (nM) | IC50 (nM) | IC50 (nM) | IC50 (nM) | |
1 |
|
++ | ||||
2 |
|
+ | + | |||
3 |
|
+ | + | + | + | |
4 |
|
++ | + | + | ||
Antigen injection | Compound Administration | ||||
Mice/ | Comp | at day-1 | from day-1 to day-7 |
Group# | group | treated | Group | TNP-F | Route | (mg/kg) | Route | Regimen |
1 | 4 | Vehicle | Antigen only | 200 uL | ip | 0 | PO | BID for |
2 | 8 | — | Antigen only | (0.5 | 0 | 7 days | ||
3 | 8 | Reference | reference | mg/ml) | 30 | |||
compound #1 | ||||||||
4 | 8 | Test | Antigen + | 1 | ||||
5 | 8 | compound | cmp | 3 | ||||
6 | 8 | 10 | ||||||
7 | 8 | 30 | ||||||
8 | 8 | 60 | ||||||
4=Marked=Full thickness defects in cortical bone, often with distortion of profile of remaining cortical surface, marked loss of medullary bone, numerous osteoclasts, ½-¾ of tibia or tarsals affected at marginal zones
5=Severe=Full thickness defects in cortical bone, often with distortion of profile of remaining cortical surface, marked loss of medullary bone, numerous osteoclasts, >¾ of tibia or tarsals affected at marginal zones, severe distortion of overall architecture
Bone Resorption (Knee)
0=Normal
1=Minimal=small areas of resorption, not readily apparent on low magnification, rare osteoclasts
2=Mild=more numerous areas of resorption, definite loss of subchondral bone involving ¼ of tibial or femoral surface (medial or lateral)
3=Moderate=obvious resorption of subchondral bone involving >¼ but <½ of tibial or femoral surface (medial or lateral)
4=Marked=obvious resorption of subchondral bone involving >½ but <¾ of tibial or femoral surface (medial or lateral)
5=Severe=distortion of entire joint due to destruction involving >¾ of tibial or femoral surface (medial or lateral)
1. Statistical analysis of body/paw weights, paw AUC parameters and histopathologic parameters were evaluated using a Student's t-test or other appropriate (ANOVA with post-test) with significance set at the 5% significance level. Percent inhibition of paw weight and AUC was calculated using the following formula:
% Inhibition=A−B/A×100
A=Mean Disease Control−Mean Normal
B=Mean Treated−Mean Normal
Compound Administration | ||||
Mice/ | from day-1 to day-7 |
Group# | group | (mg/kg) | Route | Regimen |
1 | 3 | 1 | Po | BID for |
2 | 3 | 3 | 7 days | |
3 | 3 | 10 | ||
4 | 3 | 30 | ||
5 | 3 | 60 | ||
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